Has anyone made the jump to $uper High end and were disappointed?

Two comments:
I went to my first audio show last year, the Cap Audio Fest, at one point I turned to my friend and said I was being totally influenced by my reaction to the music being played, liking the rooms where I liked the music. So absolutely recordings make a big difference.

If you are really spending $50k on individual components then I really hope you are working with a very good honest dealer. One that will give good advice and let you audition gear at home as well as ancillaries. To me that is a good way to build a system and avoid buyers remorse, at any price point.

@geoffkait Understood and sorry if I put words in your mouth. I guess my point was believe yourself. And your ears.

What @geoffkait  calls "stove piping" I, and others, call trusting our ears. It's worth a try.

+1 Wolf an everything you said cars and audio both! My used 2003 VW Passat is the single best purchase I've ever made and boutique shops run by enthusiasts make it cheap and easy to maintain. Similarly well selected and matched components will produce good sound at a variety of price points low and high.